Water → HCID 86703872, compound

HRID 593382Notes

Reaction equation

HRID 593382 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([O:13][C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9][C:8]=1[F:18].[N:19]1[CH:24]=[CH:23][C:22]([CH:25]=[O:26])=[CH:21][CH:20]=1.O>O1CCCC1.C([Mg]Cl)CCC>[F:18][C:8]1[CH:9]=[CH:10][C:11]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:12][C:7]=1[CH:25]([C:22]1[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=1)[OH:26]

Participants

7

Reactant 4

HCID 962WaterHCID 133894-PyridinecarboxaldehydeHCID 250673591-Bromo-2-fluoro-5-(trifluoromethoxy)benzeneHCID 178418339Butyllithium

Product 1

HCID 86703872HCID 86703872, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 178418265HCID 178418265, compoundSolvent

Procedure

To a solution in tetrahydrofuran (3 mL) at 0° C. of 2.3M n-butyllithium in hexanes (0.95 mL) and 2M n-butylmagnesium chloride in tetrahydrofuran (0.55 mL) is added a solution of 2-bromo-1-fluoro-4-trifluoromethoxybenzene in tetrahydrofuran (4 mL). After stirring at 0° C. for 20 minutes 4-pyridinecarboxaldehyde (193 μL) is added and the mixture stirred at room temperature for one night. After hydrolysis with water, the aqueous phase is extracted with ethyl acetate. The pooled organic extracts are washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography over silica gel (gradient heptane/ethyl acetate from 2/1 to 1/1) to give pure (2-fluoro-5-trifluoromethoxyphenyl)pyridin-4-ylmethanol.

Workup

  1. additionis added
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. washThe pooled organic extracts are washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by chromatography over silica gel (gradient heptane/ethyl acetate from 2/1 to 1/1)

Sources & evidence

ORD record
ord-616b9539b0fb419dbcfdad49c9150c27
Source dataset
uspto-grants-2016_01
Patent number
US09242959B2

Reaction notes

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